Triticonazole (Ref: RPA 400727)

Triticonazole (Ref: RPA 400727)	Last updated: 12/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A seed treatment fungicide for the control of common soil and seed-borne diseases on cereals and other crops

Example pests controlled

Common bunt; Loose smut; Covered smut; Stem & crown rots; Blights; Powdery mildew; Scab; Anthracnose

Example applications

Cereals including wheat, barley, oats, rye, triticale; Turf; Ornamentals

Efficacy & activity

Efficacy demonstrated by field trials and extensive use

Availability status

Current

Introduction & key dates

1993, first registered France

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/04/2024

UK LERAP status

None (may vary with mixtures)

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Austria/UK

Date EC 1107/2009 inclusion expires

31/04/2021

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
✓	✓	✓		✓	✓		✓	✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓		✓		✓	✓	✓	✓	✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
✓	✓		✓	✓	✓		✓

Also used in

Australia

Chemical structure

Isomerism

A chiral molecule. The technical material is a racemate comprising equal amounts of (R)- and (S)-triticonazole

Chemical formula

C₁₇H₂₀ClN₃O

Canonical SMILES

CC1(CCC(=CC2=CC=C(C=C2)Cl)C1(CN3C=NC=N3)O)C

Isomeric SMILES

CC1(CC/C(=C\C2=CC=C(C=C2)Cl)/C1(CN3C=NC=N3)O)C

International Chemical Identifier key (InChIKey)

PPDBOQMNKNNODG-NTEUORMPSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H20ClN3O/c1-16(2)8-7-14(9-13-3-5-15(18)6-4-13)17(16,22)10-21-12-19-11-20-21/h3-6,9,11-12,22H,7-8,10H2,1-2H3/b14-9-

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Triazole

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - methanol <3 g kg⁻¹ damp product

Substance origin

Synthetic

Mode of action

Inhibits sterol demethylation. Sterol biosynthesis inhibitor.

CAS RN

131983-72-7

Alternative/old CAS RN

138182-18-0

EC number

603-543-7

CIPAC number

652

US EPA chemical code

125620

PubChem CID

6537961

Molecular mass

317.82

PIN (Preferred Identification Name)

rac-(1R,5E)-5-[(4-chlorophenyl)methylidene]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol

IUPAC name

(RS)-(E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol

CAS name

(5E)-5-[(4-chlorophenyl)methylene]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Physical state

White powder

Related substances & organisms

propylene glycol

prochloraz

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Premis 25 FS
Kinto
Fungus Clear Ultra

Example products using this active

Aventis
BASF
Bayer CropScience
Scotts

Formulation and application details

Often supplied formulated as a flowable concentrate for seed treatment

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

9.3

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

120

Hexane

74500

Acetone

18200

Methanol

12600

Toluene

Melting point (°C)

137

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

180

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

1.95 X 10⁰³

Calculated

Log P

3.29

High

Bulk density (g ml⁻¹)

1.21

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

9.0 X 10^-05

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

1.2 X 10^-06

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Neutral, acidic and basic solutions: 212nm = 23879, 263nm = 25731

Surface tension (mN m⁻¹)

72.0

at 20 °C 986g/Kg

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

237

Persistent

DT₅₀ (lab at 20 °C)

246

Persistent

DT₅₀ (field)

147.7

Persistent

DT₉₀ (lab at 20 °C)

773

Very persistent

DT₉₀ (field)

580.6

DT₅₀ modelling endpoint

Note

EU 2018 dossier lab studies DT₅₀ (normalised) range 109-565 days, DT₉₀ (actual) range 381- >1000 days, Soils=14; Field studies DT₅₀ (actual) range 36.1-242 days, DT₉₀ (actual) range 329-803 days, Soils=9

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

300

Stable

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

7.4

Non-persistent

Note

Stable at all relevant pHs

Water-sediment DT₅₀ (days)

Stable

Water phase only DT₅₀ (days)

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Moderately mobile

K_oc

374

Notes and range

Freundlich

K_f

6.36

Slightly mobile

K_foc

569.8

¹/_n

0.900

Notes and range

EU 2018 dossier kf range 3.67-13.4 mL g⁻¹, K_foc range 290-871 mL g⁻¹, ¹/_n range 0.848-0.940, Soils=10

pH sensitivity

Yes

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.70

Calculated

Transition state

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

2.19 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

(1R,3R,E)-3-(4-chlorobenzylidene)-5,5-dimethyl-1-((1H)-1,2,4-triazol-1-ylmethyl)-cyclopentan-1,3-diol (Ref: RPA 406341)

Soil

0.202

Major fraction, Relevant

(E)-2-(4-chlorobenzylidene)-5,5-dimethyl-1-((1H)-1,2,4-triazol-1-ylmethyl)-cyclopentan-1,3-diol (Ref: RPA 404766)

Soil

0.099

Minor fraction, Relevant

2-chloro-5((E)-((2RS)-2-hydroxy-3,3-dimethyl-2-(1H-1,2,4-triazole-1-ylmethyl)cyclopentylidenc)methyl)phenol (Ref: RPA 407922)

Soil

0.128

Major fraction, Not relevant

(1RS, 5Z)-5-(4-chlorobenzylidence)-2-2-dimethyl-1-(1H-1,2,4-triazole-1-ylmethyl)cyclopentanol (Ref: RPA 406203)

Soil

0.110

Major fraction, Relevant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 21

Rat

High

(ppm diet)

> 250

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

48.4

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 693 mg kg bw⁻¹ day⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

19.5

Colinus virginianus NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 3.6

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.01

Oncorhynchus mykiss 28 day

Moderate

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

9.0

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.092

Daphnia magna

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.08

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

1.1

Lemna gibba

Moderate

Non-target plants

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 1.0

Pseudokirchneriella subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 92.26

Apis mellifera

Moderate

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 500

Eisenia foetida corr

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

> 125

Eisenia foetida 56day corr

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Mortality [Dose: 0.1 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

0 / 0

Mortality / Fecundity [Dose: 0.1 kg ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 0.167 mg kg⁻¹ dw soil 28 days

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.61

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.025

Dog SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.05

Dog SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

0.05

Rabbit SF=100

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.025

Dog 1 year SF=100

Dermal penetration studies (%)

1-3

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Possible liver and adrenals toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Environment: H411

EC Risk Classification

N - Dangerous for the environment: R51, R53

EC Safety Classification

S61

WHO Classification

III (Slightly hazardous)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

triticonazole

French

triticonazole

German

Triticonazol

Danish

triticonazol

Italian

triticonazolo

Spanish

triticonazol

Greek

Polish

tritikonazol

Swedish

tritikonazol

Hungarian

tritikonazol

Dutch

Record last updated:	12/01/2021
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242